EP2076478B1 - Verfahren zur herstellung fluorierter olefine - Google Patents

Verfahren zur herstellung fluorierter olefine Download PDF

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Publication number
EP2076478B1
EP2076478B1 EP07863530A EP07863530A EP2076478B1 EP 2076478 B1 EP2076478 B1 EP 2076478B1 EP 07863530 A EP07863530 A EP 07863530A EP 07863530 A EP07863530 A EP 07863530A EP 2076478 B1 EP2076478 B1 EP 2076478B1
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Prior art keywords
catalyst
reaction
stream
conversion
fluorinated
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English (en)
French (fr)
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EP2076478A1 (de
EP2076478B2 (de
Inventor
Michael Vanderpuy
George R. Cook
Peter H. Scheidle
Kevin D. Ulrich
Haiyou Wang
Hsueh Sung Tung
Ian Shankland
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Honeywell International Inc
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Honeywell International Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1

Definitions

  • 1,2,3,3,3-Pentafluoropropene-1 is hydrogenated using the same reactor as in Example 1 using a feed rate of 14.6 lb/h for a total of 64 hours.
  • the average hydrogen feed rate is 25 liters per minute.
  • Samples are taken at various points along the series of reactors to follow the percent conversion and selectivity. After the second reactor, the conversion is about 54%. While after the fourth reactor, the conversion is 100% with the selectivity for CF 3 CHFCH 2 F of 98%.
  • the temperature of the gases immediately exiting the reactors is 99°C for the first reactor, 95°C for the second reactor, 173°C for the third reactor, and 104°C for the fourth reactor.
  • the maximum temperature in any reactor is about 240°C.
  • the first bath is maintained at 59°C
  • the second bath is maintained at 116°C.
  • the column bottoms containing sulfuric acid and HF are recycled back to the extraction tower until the HF concentration is greater than 10 wt% HF. Subsequently, the sulfuric acid and HF mixture is charged into a 2 gallon Teflon ® vessel. The mixture is heated to about 140°C to vaporize and flash off HF, which is collected. The collected HF product contains 6000 ppm water and 217 ppm sulfur. The sulfuric acid contains about 500 ppm of total organic carbon.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (8)

  1. Verfahren zur Herstellung eines fluorierten Olefins als Produkt, bei dem man:
    (a) einen Einsatzstrom, der fluoriertes Olefin und Wasserstoff als Reaktanten umfasst, mit einer ersten Menge eines Katalysators kontaktiert, wobei die Reaktanten mit einer ersten Umwandlungsrate in ein Hydrofluoralkan umgewandelt werden und ein erster Ausgangsstrom, der das Hydrofluoralkan, nicht umgesetztes fluoriertes Olefin und Wasserstoff umfasst, anfällt;
    (b) den ersten Ausgangsstrom mit einer zweiten Menge eines Katalysators kontaktiert, wobei das nicht umgesetzte fluorierte Olefin mit einer zweiten Umwandlungsrate in ein Hydrofluoralkan umgewandelt wird, wobei die zweite Katalysatormenge größer ist als die erste Katalysatormenge und die zweite Umwandlungsrate größer ist als die erste Umwandlungsrate;
    (c) mindestens einen Teil des Hydrofluoralkans aus dem Kontaktierungsschritt (b) dehydrohalogeniert, wobei ein Produktstrom, der ein fluoriertes Olefin und HF als Produkt umfasst, anfällt; und
    (d) gegebenenfalls das HF von dem Produktstrom trennt.
  2. Verfahren nach Anspruch 1, bei dem man in Schritt (d) ferner mindestens einen Teil des Produktstroms mit Schwefelsäure kontaktiert, wobei HF aus dem Produktstrom extrahiert wird.
  3. Verfahren nach Anspruch 2, bei dem bei dem Kontaktieren in Schritt (d) ein Schwefelsäure-Austragsstrom, der mindestens einen Teil des HF aus dem Produktstrom enthält, anfällt und man bei dem Verfahren ferner mindestens einen Teil des Schwefelsäure-Ausgangsstroms durch einen Extraktionsturm rezykliert.
  4. Verfahren nach Anspruch 1, bei dem die Reaktanten ein Fluorpropen mit drei bis sechs Fluorsubstituenten umfassen.
  5. Verfahren nach Anspruch 1, bei dem das Hydrofluoralkan Chlortrifluorpropan (H-FCKW 244), Pentafluorpropan (H-FKW 245) und/oder (H-FKW 236) umfasst.
  6. Verfahren nach Anspruch 1, bei dem das Produkt F2C=CFCF3 und/oder CFH=CFCF3 umfasst.
  7. Verfahren nach Anspruch 1, bei dem die Umwandlungsschritte (a) und (b) jeweils die Verwendung von kohlenstoffgeträgertem Palladium umfassen.
  8. Verfahren nach Anspruch 1, bei dem der Dehydrohalogenierungsschritt eine katalysierte Reaktion unter Beteiligung eines Katalysators aus der Gruppe bestehend aus einem oder mehreren fluorierten Metalloxiden, Metallfluoriden, kohlenstoffgeträgerten Übergangsmetallen und Kombinationen davon umfasst.
EP07863530.7A 2006-10-27 2007-10-26 Verfahren zur herstellung fluorierter olefine Active EP2076478B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/588,464 US7560602B2 (en) 2005-11-03 2006-10-27 Process for manufacture of fluorinated olefins
PCT/US2007/082601 WO2008057794A1 (en) 2006-10-27 2007-10-26 Process for the manufacture of fluorinated olefins

Publications (3)

Publication Number Publication Date
EP2076478A1 EP2076478A1 (de) 2009-07-08
EP2076478B1 true EP2076478B1 (de) 2012-10-03
EP2076478B2 EP2076478B2 (de) 2020-11-25

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ID=39201461

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07863530.7A Active EP2076478B2 (de) 2006-10-27 2007-10-26 Verfahren zur herstellung fluorierter olefine

Country Status (8)

Country Link
US (2) US7560602B2 (de)
EP (1) EP2076478B2 (de)
JP (1) JP5588174B2 (de)
KR (2) KR20140090702A (de)
CN (1) CN101553453B (de)
ES (1) ES2394870T5 (de)
RU (1) RU2457195C2 (de)
WO (1) WO2008057794A1 (de)

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KR20090071510A (ko) 2009-07-01
CN101553453B (zh) 2013-05-29
US20070179324A1 (en) 2007-08-02
ES2394870T5 (es) 2021-07-27
RU2008122213A (ru) 2010-04-27
WO2008057794A1 (en) 2008-05-15
US7786333B2 (en) 2010-08-31
RU2457195C2 (ru) 2012-07-27
US7560602B2 (en) 2009-07-14
ES2394870T3 (es) 2013-02-06
JP2010508294A (ja) 2010-03-18
KR20140090702A (ko) 2014-07-17
US20090209791A1 (en) 2009-08-20
CN101553453A (zh) 2009-10-07
JP5588174B2 (ja) 2014-09-10
EP2076478A1 (de) 2009-07-08
EP2076478B2 (de) 2020-11-25

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